| Game # | Date | Start Time | Home | Visitor | Diamond |
| 1 | 08/07/2026 | 6:00 PM | HH - White Sox | Milton A's | Trafalgar Sports Park - 1 |
| 2 | 08/07/2026 | 6:00 PM | Milton Red Sox | Milton Yankees | Trafalgar Sports Park - 2 |
| 3 | 08/07/2026 | 8:30 PM | Oakville Red Sox | HH - Orioles | Trafalgar Sports Park - 1 |
| 4 | 08/07/2026 | 8:30 PM | HH - Athletics | Milton Blue Jays | Trafalgar Sports Park - 2 |
| 5 | 08/08/2026 | 9:00 AM | HH - White Sox | HH - Yankees | Trafalgar Sports Park - 1 |
| 6 | 08/08/2026 | 9:00 AM | Milton Red Sox | Milton A's | Trafalgar Sports Park - 2 |
| 7 | 08/08/2026 | 10:00 AM | Oakville Red Sox | Milton Yankees | Trafalgar Sports Park - 4 |
| 8 | 08/08/2026 | 12:00 PM | HH - Orioles | Milton Blue Jays | Trafalgar Sports Park - 1 |
| 9 | 08/08/2026 | 12:00 PM | HH - Yankees | HH - Athletics | Trafalgar Sports Park - 2 |
| 10 | 08/08/2026 | 3:30 PM | Seed 1 | Seed 8/9 | Trafalgar Sports Park - 1 |
| 11 | 08/08/2026 | 3:30 PM | Seed 4 | Seed 5 | Trafalgar Sports Park - 2 |
| 12 | 08/08/2026 | 3:30 PM | Seed 2 | Seed 7 | Trafalgar Sports Park - 4 |
| 13 | 08/08/2026 | 6:00 PM | Seed 3 | Seed 6 | Trafalgar Sports Park - 1 |
| 14 | 08/09/2026 | 10:00 AM | QF 1 | QF 2 | Eighth Line Park - 1 |
| 15 | 08/09/2026 | 10:00 AM | QF 3 | QF 4 | Trafalgar Sports Park - 2 |
| 16 | 08/09/2026 | 1:30 PM | Final | Final | Trafalgar Sports Park - 2 |